BG105620A - Заместени пиразоли като инхибитори на р38 киназата - Google Patents

Info

Publication number

BG105620A

BG105620A BG105620A BG10562001A BG105620A BG 105620 A BG105620 A BG 105620A BG 105620 A BG105620 A BG 105620A BG 10562001 A BG10562001 A BG 10562001A BG 105620 A BG105620 A BG 105620A

Authority

BG

Bulgaria

Prior art keywords

alkyl

aryl

hydroxy

heterocyclyl

haloalkyl

Prior art date

1998-11-20

Links

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• 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 17
• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 212
• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims abstract description 22
• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 22
• -1 hydrido, hydroxy Chemical group 0.000 claims description 946
• 125000000217 alkyl group Chemical group 0.000 claims description 376
• 125000003118 aryl group Chemical group 0.000 claims description 254
• 125000000623 heterocyclic group Chemical group 0.000 claims description 237
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 219
• 125000003545 alkoxy group Chemical group 0.000 claims description 184
• 125000001188 haloalkyl group Chemical group 0.000 claims description 181
• 150000003254 radicals Chemical class 0.000 claims description 175
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 126
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 116
• 125000000304 alkynyl group Chemical group 0.000 claims description 115
• 125000001145 hydrido group Chemical group *[H] 0.000 claims description 115
• 125000005843 halogen group Chemical group 0.000 claims description 114
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 111
• 125000003342 alkenyl group Chemical group 0.000 claims description 102
• 229910052739 hydrogen Inorganic materials 0.000 claims description 102
• 125000003282 alkyl amino group Chemical group 0.000 claims description 99
• 239000001257 hydrogen Substances 0.000 claims description 99
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 98
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 98
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 89
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 88
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 87
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 87
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 85
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 84
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 83
• 239000000460 chlorine Substances 0.000 claims description 83
• 229910052801 chlorine Inorganic materials 0.000 claims description 83
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 80
• 125000004104 aryloxy group Chemical group 0.000 claims description 73
• 150000003839 salts Chemical class 0.000 claims description 72
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 71
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 68
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
• 125000004414 alkyl thio group Chemical group 0.000 claims description 65
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 58
• 125000001424 substituent group Chemical group 0.000 claims description 55
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 54
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 125000001769 aryl amino group Chemical group 0.000 claims description 53
• 229910052731 fluorine Inorganic materials 0.000 claims description 53
• 239000011737 fluorine Substances 0.000 claims description 53
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 52
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 50
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 50
• 229910052794 bromium Inorganic materials 0.000 claims description 50
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 46
• 125000004076 pyridyl group Chemical group 0.000 claims description 45
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 41
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 38
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 38
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 37
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 36
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 35
• 235000010290 biphenyl Nutrition 0.000 claims description 34
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 33
• 125000002947 alkylene group Chemical group 0.000 claims description 32
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
• 239000004305 biphenyl Substances 0.000 claims description 32
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 31
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 27
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 26
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 26
• 150000001721 carbon Chemical group 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 25
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 25
• 150000002367 halogens Chemical class 0.000 claims description 25
• 125000001624 naphthyl group Chemical group 0.000 claims description 25
• 125000003386 piperidinyl group Chemical group 0.000 claims description 25
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 25
• 125000000335 thiazolyl group Chemical group 0.000 claims description 24
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 23
• 125000005110 aryl thio group Chemical group 0.000 claims description 23
• 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 23
• PCPQWYHRMVULIX-UHFFFAOYSA-P [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;dinitrate Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 PCPQWYHRMVULIX-UHFFFAOYSA-P 0.000 claims description 22
• 208000035475 disorder Diseases 0.000 claims description 22
• 238000000034 method Methods 0.000 claims description 22
• 125000005494 pyridonyl group Chemical group 0.000 claims description 22
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 21
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 20
• 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 20
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 19
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 19
• 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 19
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 18
• 229930194542 Keto Natural products 0.000 claims description 17
• 125000005122 aminoalkylamino group Chemical group 0.000 claims description 17
• 125000005128 aryl amino alkyl group Chemical group 0.000 claims description 17
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
• 125000000468 ketone group Chemical group 0.000 claims description 17
• 125000004193 piperazinyl group Chemical group 0.000 claims description 17
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 16
• 125000002252 acyl group Chemical group 0.000 claims description 15
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 15
• UNLBRWACURAHRZ-UHFFFAOYSA-N oxo-[[1-[[5-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methyl]thiophen-2-yl]methyl]pyridin-4-ylidene]methyl]azanium;diperchlorate Chemical compound [O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C1=CC(=C[NH+]=O)C=CN1CC(S1)=CC=C1CN1C=CC(=C[NH+]=O)C=C1 UNLBRWACURAHRZ-UHFFFAOYSA-N 0.000 claims description 15
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 14
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 14
• 125000004171 alkoxy aryl group Chemical group 0.000 claims description 14
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 14
• 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 14
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 14
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 14
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 14
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 14
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 13
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
• 125000001091 aminosulfinyl group Chemical group [H]N([H])S(*)=O 0.000 claims description 11
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• 239000004215 Carbon black (E152) Substances 0.000 claims description 10
• 206010061218 Inflammation Diseases 0.000 claims description 10
• 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 229930195733 hydrocarbon Natural products 0.000 claims description 10
• 150000002430 hydrocarbons Chemical class 0.000 claims description 10
• 230000004054 inflammatory process Effects 0.000 claims description 10
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 9
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 9
• 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 8
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 8
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 8
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
• 125000005108 alkenylthio group Chemical group 0.000 claims description 6
• 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 6
• 125000005109 alkynylthio group Chemical group 0.000 claims description 6
• 125000002431 aminoalkoxy group Chemical group 0.000 claims description 6
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 6
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 6
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
• 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 6
• 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 5
• 125000005001 aminoaryl group Chemical group 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 5
• 206010035664 Pneumonia Diseases 0.000 claims description 4
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 206010006895 Cachexia Diseases 0.000 claims description 3
• 201000005569 Gout Diseases 0.000 claims description 3
• 235000004431 Linum usitatissimum Nutrition 0.000 claims description 3
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
• 201000008482 osteoarthritis Diseases 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• 125000003944 tolyl group Chemical group 0.000 claims description 3
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
• 201000001320 Atherosclerosis Diseases 0.000 claims description 2
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
• 208000011231 Crohn disease Diseases 0.000 claims description 2
• 201000004681 Psoriasis Diseases 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
• 208000007536 Thrombosis Diseases 0.000 claims description 2
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 2
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
• 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 2
• 210000000988 bone and bone Anatomy 0.000 claims description 2
• 230000000747 cardiac effect Effects 0.000 claims description 2
• 238000006243 chemical reaction Methods 0.000 claims description 2
• 230000001684 chronic effect Effects 0.000 claims description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 230000001419 dependent effect Effects 0.000 claims description 2
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 208000027866 inflammatory disease Diseases 0.000 claims description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 52
• 125000004450 alkenylene group Chemical group 0.000 claims 28
• 229910052740 iodine Inorganic materials 0.000 claims 27
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 26
• 239000011630 iodine Substances 0.000 claims 26
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 21
• 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims 17
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims 14
• 239000002184 metal Substances 0.000 claims 9
• 229910052751 metal Inorganic materials 0.000 claims 9
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 6
• JILXUIANNUALRZ-UHFFFAOYSA-N n',n'-diethylbutane-1,4-diamine Chemical compound CCN(CC)CCCCN JILXUIANNUALRZ-UHFFFAOYSA-N 0.000 claims 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
• 230000001105 regulatory effect Effects 0.000 claims 6
• 238000006467 substitution reaction Methods 0.000 claims 6
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 5
• 229920000180 alkyd Polymers 0.000 claims 5
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 5
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
• 125000004419 alkynylene group Chemical group 0.000 claims 4
• 125000006294 amino alkylene group Chemical group 0.000 claims 4
• 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims 4
• HGUZQMQXAHVIQC-UHFFFAOYSA-N n-methylethenamine Chemical group CNC=C HGUZQMQXAHVIQC-UHFFFAOYSA-N 0.000 claims 4
• JSBBMMHTNIUVTC-UHFFFAOYSA-N 2-hydroxyethanone Chemical group OC[C]=O JSBBMMHTNIUVTC-UHFFFAOYSA-N 0.000 claims 3
• 230000002378 acidificating effect Effects 0.000 claims 3
• 125000002877 alkyl aryl group Chemical group 0.000 claims 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
• 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims 3
• 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims 3
• 239000002904 solvent Substances 0.000 claims 3
• TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
• 241000208202 Linaceae Species 0.000 claims 2
• 125000006326 aryl hydrazinyl group Chemical group 0.000 claims 2
• 239000001273 butane Substances 0.000 claims 2
• 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 2
• 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
• 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
• KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 2
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
• DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 claims 2
• 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
• 230000010410 reperfusion Effects 0.000 claims 2
• ZEMCGIDMAMIJLF-UHFFFAOYSA-N 1-benzyl-2-phenylhydrazine Chemical compound C=1C=CC=CC=1CNNC1=CC=CC=C1 ZEMCGIDMAMIJLF-UHFFFAOYSA-N 0.000 claims 1
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
• NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 claims 1
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
• HSPRAJKYYHMMLK-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(=N)N(C(=N)N)C(=C=CNC(=N)N)NC(=N)N Chemical group C(C1=CC=CC=C1)NC(=N)N(C(=N)N)C(=C=CNC(=N)N)NC(=N)N HSPRAJKYYHMMLK-UHFFFAOYSA-N 0.000 claims 1
• WVXDALCQQYPHCG-UHFFFAOYSA-N CNC=CNC=C=CNCC Chemical group CNC=CNC=C=CNCC WVXDALCQQYPHCG-UHFFFAOYSA-N 0.000 claims 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
• 101150065749 Churc1 gene Proteins 0.000 claims 1
• 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 claims 1
• 206010018364 Glomerulonephritis Diseases 0.000 claims 1
• 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 claims 1
• SJBVFIWZGBGAEX-UHFFFAOYSA-N NC(=N)NC=C=CNC(N)=N Chemical group NC(=N)NC=C=CNC(N)=N SJBVFIWZGBGAEX-UHFFFAOYSA-N 0.000 claims 1
• 102100038239 Protein Churchill Human genes 0.000 claims 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
• 150000001241 acetals Chemical class 0.000 claims 1
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
• 239000002253 acid Substances 0.000 claims 1
• 239000003513 alkali Substances 0.000 claims 1
• 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims 1
• 150000003973 alkyl amines Chemical class 0.000 claims 1
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 1
• 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims 1
• 125000000732 arylene group Chemical group 0.000 claims 1
• ZUCWUADHUDQXHX-UHFFFAOYSA-N but-1-en-2-amine Chemical group CCC(N)=C ZUCWUADHUDQXHX-UHFFFAOYSA-N 0.000 claims 1
• 125000006309 butyl amino group Chemical group 0.000 claims 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
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